Hotels with Pools in Pittsfield

Your Gateway to Relaxation and Adventure in the Heart of the Berkshires Discover the perfect home base for your next getaway at our brand-new hotel, nestled in the scenic Berkshires of Western...

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Christian

From

Germany

Brand new Hotel opened in July 2025, great breakfast, nice management.

Featuring an indoor swimming pool and a fitness centre, Berkshire Mountain Lodge is located in Pittsfield. Free WiFi access is available in this lodge.

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Graeme

From

United Kingdom

Best suite we stayed in on a 3 week trip, so finishing on a high. Very large suite with comfy beds and seating, well equipped kitchen and great location for local exploring

Hilton Garden Inn Lenox/Pittsfield/Berkshires offers accommodation in Pittsfield. The hotel has a fitness centre and indoor pool, and guests can enjoy a meal at the restaurant or a drink at the bar.

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MARY

From

Ireland

Liked there was an excellent restaurant on site.

Located in the heart of the Berkshire Mountains, this family-owned motel features an outdoor pool and free Wi-Fi. The Bousquet Ski Area is only an 8-minute drive away.

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Yana

From

United States

I am always happy with my stays at the Berkshire Inn. The bed is super comfortable. I love that there is a bathtub. It's quiet and the staff are nice and accommodating. Great value. Recommended.

Welcome to the Holiday Inn and Suites Pittsfield-Berkshires Centrally located in downtown Pittsfield Massachusetts.

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Andrea

From

United Kingdom

The pool was a real bonus! The on-site restaurant was a delight - excellent food and amusing bartender. The central location was perfect for my needs. Would stay there again without hesitation - lovely hotel.

Nestled on a 111-acre wildlife sanctuary and surrounded by the beauty of the Berkshires, The Yankee, Trademark Collection by Wyndham provides a welcoming stay by the famous Appalachian Trail in...

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Sally

From

Australia

Excellent place to stay, comfortable, clean and quiet. The customer service was flawless and we were very impressed. Hubby loved his breakfast on the second floor, and said everything was flavourful and delicious. Thank you for a great stay it was a pleasure to stay with you.

This Lenox, Massachusetts hotel is situated only a short distance from area attractions, including historic Lenox town centre and features a variety of free amenities along with comfortable and modern...

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Zachi

From

Israel

The rooms, great rich breakfast, staff accommodating. Modern hotel with perfect upkeep and comfortable bed.

Boasting a garden, Howard Johnson by Wyndham Lenox is situated in Lenox in the Massachusetts region, 7.4 km from Cranwell Spa & Golf Club and 7.7 km from Tanglewood Musical Center.

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Elona

From

United States

The room was newly renovated. It was very nice. And the beds were very comfortable. And it was very clean. I also want to say, that Sam was a great host! He's very friendly and helpful. I wanted extra pillows, and he went, right then and got two of them. He is an excellent Host!!

Element Lenox Berkshires in Lenox has 3-star accommodation with a terrace and a bar. Featuring a restaurant, the property also has free bikes, as well as an indoor pool and a fitness centre.

C

Cheek

From

United Kingdom

The facilities were amazing - fab indoor pool, excellent, large well equipped gym. In house launderette. Hotel is new so was beautifully clean. Ample parking.

Situated in Williamstown, 36 km from Cranwell Spa & Golf Club, Berkshire Valley Inn features accommodation with a seasonal outdoor swimming pool, free private parking, a shared lounge and barbecue...

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ANNA-MARIA

From

United States

Excellent location. We appreciated the cleanliness, beautiful decorating, attention to detail. It is obvious that the owner put a lot of thought, attention, and care into the property. I appreciated the low amount of plastics and nice breakfast. The pool was well-kept and my kids had an awesome time!